Stereoselective dehalogenation of (Z)-1-halo-1-alkenyldialkylborane with tributyltin hydride: The behavior of tributyltin hydride as a hydride donor

Article abstract of DOI:10.1016/S0040-4039(96)02324-6

The reaction of (Z)-1-halo-1-alkenyldialkylborane (1) with tributyltin hydride (n-Bu₃SnH) at 0°C or room temperature results in reductive removal of the halogen atom to afford (E)- or (Z)-1-alkenyldialkylborane whose stereochemistry depends on the dialkylboryl group and the alkenyl group of 1.